I think I get more questions about jeans than any other item of clothing. We all know how difficult it can be to find the perfect pair, and it’s even more difficult to work out which style works for you. Personally, I love all jeans styles, except maybe the low-rise boot cut from the early 2000s, especially when worn with a visible thong and a handkerchief top. Fine if you were Beyonce in Destiny’s Child, not quite the same if you were Brenda from Dorking. Some trends are best left in the past. But others (as we will discuss later) are quite a welcome comeback.
I’ve had a look back at photos of me wearing some of my favourite jeans to give you a few ideas on how to style them. As I have all these pairs, I can give you some sizing advice. I also get a lot of questions on which shoes to wear with which jeans. I’m not saying I get it right all the time, but I was pretty happy with these looks so let’s dive straight in…
STRAIGHT LEG JEANS
Here’s one from pre-Covid (I had short hair back then too! I’ve recently reverted back to this style; it’s cut precious hair-drying and styling time in half). These jeans are super old and from River Island. They don’t sell them anymore, unfortunately, but the Hush Agnes straight-leg ones are very similar. I have these in the grey and they’re true to size and with a nice bit of stretch too. A little jeans tip for you: have a look at the material composition, especially if you are buying online and don’t have the luxury of trying before buying. If there’s elastane in them, you’re probably ok to take your regular size or even go down a size as they will stretch out. If jeans are 100% cotton, there won’t be much ‘give’ in them.
Straight-leg jeans are probably the easiest style to wear. I like to roll up the hem of my straight-leg jeans and wear them with boots that sit just under the hem. In the summer, trainers work a treat – as do Converse hi-tops and flat sandals.
WIDE LEG JEANS
It was only really last year that I got into wide-leg jeans. I don’t know why I didn’t go for them before. Maybe because they really deserve a pair of heels and I tend to shy away from those, BUT a good block-heel boot is easy to get on board with. A decent pair of wide-leg jeans will elongate your legs and make you look taller and slimmer. I have three pairs (all high street) but I think these from Karen Millen are my favourite. For reference I am 5’7 and they hit at just the right length so they don’t drag on the floor. They also have a zip front so there’s no added bulk on the tummy area. High cut but not TOO high. Take your regular size in these. I also have a pair from M&S, similar to these. Also true to size.
BARREL / TAPERED JEANS
They could also be termed as ‘mom’ jeans: high-waisted, tapered at the leg. These probably work best on hourglass figures (slim waist, curvier thighs). That’s not me, but I still love them, proving that you can largely ignore what’s ‘supposed’ to suit your figure. Again, roll up the hem, wear with a fancy sock and a chunky trainer. It kind of balances out some of the volume. I rarely wear these with boots. I’m wearing the COS tapered-leg jeans, and I’d say they’re true to size but there’s no stretch, so size up if you fancy a slightly looser fit.
90’S BAGGY JEANS
These could divide the room, but I’m really into the 90s baggy style again. Super casual, but also super comfortable. Not great in the rain, so you do have to check the forecast before you leave the house in these. Surely we all remember the curse of the soggy hems in the mid-90s when we strutted out to the local indie disco in our Joe Bloggs, our Happy Mondays T‑shirt and our Adidas Gazelles (also having another moment btw), then got caught in a downpour waiting for the bus home. Not to mention the debris from the club floor languishing on the hem of your jeans. These days, look for a pair that doesn’t drag too much on the floor! I like to wear mine with Nike Air Jordans and a baggy jumper. I’m wearing the Uniqlo baggy jeans above. I got my regular size as I wanted them loose on the waist, but size down if you want a closer fit. The Hush ones are true to size.
SLIM LEG JEANS
Are skinny jeans over? I would say don’t give them away just yet, especially your black ones. There will always be a place in my wardrobe for skinny black jeans. My favourite ever are the Paige Hoxton jeans. Not skin-tight, but more of a slim-leg style. They aren’t cheap, but I’ve had mine for five years now and they have been washed and worn loads, yet they’re still a perfect fit and haven’t faded at all. Super stretchy and comfy. Take your regular size. Looking back on old pics, I also saw how much I have worn these DM boots. The more you wear them, the more comfortable they get. For breaking in tips, see this post.
Possibly saving the best for last, I think these Raey ‘Dad’ jeans are probably my most worn pair. They’re a loose-fitting boyfriend style, great in the winter with hi-tops and also perfect in the summer with chunky sandals. Heed my advice if you like the look of these and SIZE DOWN! They come up really big. I have them in size 28 and I’m a 12 but they’re still loose and, depending on the size of my stomach at any given time, I do have to wear a belt sometimes. Also, don’t get the light wash, as the denim is totally different and frankly, not as good. These from Agolde are my other favourites, size down on these too. On sale at a huge discount at Flannels right now.
I hope this was helpful and that it’s given you some jeans inspiration.